HCID 117627866, compound → HCID 89533660, compound

HRID 1050978Notes

Reaction equation

HRID 1050978 reaction equation
[OH:1][C:2]1[C:18]([N+:19]([O-])=O)=[CH:17][CH:16]=[CH:15][C:3]=1[C:4]([N:6]1[CH2:10][CH2:9][CH2:8][C@@H:7]1[C:11]([O:13][CH3:14])=[O:12])=[O:5].[H][H]>CO.[Pd]>[NH2:19][C:18]1[C:2]([OH:1])=[C:3]([CH:15]=[CH:16][CH:17]=1)[C:4]([N:6]1[CH2:10][CH2:9][CH2:8][C@@H:7]1[C:11]([O:13][CH3:14])=[O:12])=[O:5]

Participants

5

Reactant 2

HCID 117627866HCID 117627866, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 89533660HCID 89533660, compoundYield 74%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 4.03 g (13.63 mmol; 1.0 eq) of methyl (R)-1-(2-hydroxy-3-nitrobenzoyl)pyrrolidine-2-carboxylate in 50 ml of methanol was stirred at hydrogen atmospheric pressure in the presence of 390 mg (10% by weight) of palladium on carbon at 10% for 3 days. The reaction medium was filtered through celite, rinsed with methanol and evaporated. The residue was chromatographed on silica gel (200 g prepacked column) eluted with heptane/ethyl acetate (gradient). 2.65 g of methyl (R)-1-(3-amino-2-hydroxybenzoyl)pyrrolidine-2-carboxylate were obtained in the form of a yellow oil. Yield=74%.

Workup

  1. filtrationThe reaction medium was filtered through celite
  2. washrinsed with methanol
  3. customevaporated
  4. customThe residue was chromatographed on silica gel (200 g prepacked column)
  5. washeluted with heptane/ethyl acetate (gradient)

Sources & evidence

ORD record
ord-17d6a9f34b794b92bbe613500b7a4894
Source dataset
uspto-grants-2016_07
Patent number
US09388149B2

Reaction notes

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